diff --git a/pkg/filesystem/path/builder.go b/pkg/filesystem/path/builder.go
index 80be90aa..8ca6c9ff 100644
--- a/pkg/filesystem/path/builder.go
+++ b/pkg/filesystem/path/builder.go
@@ -109,14 +109,23 @@ func (b *Builder) GetWindowsString(format WindowsPathFormat) (string, error) {
 		prefix = "\\"
 	}
 
-	// Emit trailing slash in case the path refers to a directory,
-	// or a dot or slash if the path is empty. The suffix is been
-	// constructed by platform-independent code that uses forward
-	// slashes. To construct a Windows path we must use a
+	// If the path refers to a directory we should emit a trailing slash,
+	// and since the suffix has been constructed by platform-independent code
+	// that uses forward slashes we need to convert the path to use a
 	// backslash.
+	//
+	// Unfortunately, a trailing backslash is not a valid pathname component:
+	// https://learn.microsoft.com/en-us/openspecs/windows_protocols/ms-fscc/ffb795f3-027d-4a3c-997d-3085f2332f6f
+	// Instead we emit `\.` and rely on win32 path normalization. However,
+	// for WindowsPathFormatDevicePath we cannot do this as device paths
+	// bypass win32 path normalization so have to just emit a backlash.
 	suffix := b.suffix
 	if suffix == "/" {
-		suffix = "\\"
+		if format == WindowsPathFormatDevicePath {
+			suffix = "\\"
+		} else {
+			suffix = "\\."
+		}
 	}
 	out.WriteString(suffix)
 	return out.String(), nil
diff --git a/pkg/filesystem/path/builder_test.go b/pkg/filesystem/path/builder_test.go
index 33ef2004..157b1c5a 100644
--- a/pkg/filesystem/path/builder_test.go
+++ b/pkg/filesystem/path/builder_test.go
@@ -63,14 +63,14 @@ func TestBuilder(t *testing.T) {
 		for _, data := range [][]string{
 			{".", "."},
 			{"..", ".."},
-			{"/", "\\"},
+			{"/", "\\."},
 			{"hello", "hello"},
-			{"hello/", "hello\\"},
+			{"hello/", "hello\\."},
 			{"hello/..", "hello\\.."},
-			{"/hello/", "\\hello\\"},
+			{"/hello/", "\\hello\\."},
 			{"/hello/..", "\\hello\\.."},
 			{"/hello/../world", "\\hello\\..\\world"},
-			{"/hello/../world/", "\\hello\\..\\world\\"},
+			{"/hello/../world/", "\\hello\\..\\world\\."},
 			{"/hello/../world/foo", "\\hello\\..\\world\\foo"},
 		} {
 			p := data[0]
@@ -92,16 +92,16 @@ func TestBuilder(t *testing.T) {
 
 	t.Run("WindowsIdentity", func(t *testing.T) {
 		for _, p := range []string{
-			"C:\\",
-			"C:\\hello\\",
+			"C:\\.",
+			"C:\\hello\\.",
 			"C:\\hello\\..",
 			"C:\\hello\\..\\world",
-			"C:\\hello\\..\\world\\",
+			"C:\\hello\\..\\world\\.",
 			"C:\\hello\\..\\world\\foo",
 			"C:\\hello\\..\\world\\foo",
-			"\\\\server\\share\\hello\\",
+			"\\\\server\\share\\hello\\.",
 			"\\\\server\\share\\hello\\..\\world",
-			"\\\\server\\share\\hello\\..\\world\\",
+			"\\\\server\\share\\hello\\..\\world\\.",
 			"\\\\server\\share\\hello\\..\\world\\foo",
 		} {
 			t.Run(p, func(t *testing.T) {
@@ -146,19 +146,19 @@ func TestBuilder(t *testing.T) {
 	t.Run("WindowsParseCasing", func(t *testing.T) {
 		for _, data := range [][]string{
 			{"./bar", "bar"},
-			{"./bar\\", "bar\\"},
-			{"c:", "C:\\"},
-			{"c:.", "C:\\"},
+			{"./bar\\", "bar\\."},
+			{"c:", "C:\\."},
+			{"c:.", "C:\\."},
 			{"c:Hello", "C:\\Hello"},
-			{"c:\\", "C:\\"},
-			{"c:\\.", "C:\\"},
-			{"c:\\Hello\\", "C:\\Hello\\"},
-			{"c:\\Hello\\.", "C:\\Hello\\"},
+			{"c:\\", "C:\\."},
+			{"c:\\.", "C:\\."},
+			{"c:\\Hello\\", "C:\\Hello\\."},
+			{"c:\\Hello\\.", "C:\\Hello\\."},
 			{"c:\\Hello\\..", "C:\\Hello\\.."},
 			{"c:\\Hello\\.\\world", "C:\\Hello\\world"},
 			{"c:\\Hello\\..\\world", "C:\\Hello\\..\\world"},
 			{"c:\\Hello\\..\\world", "C:\\Hello\\..\\world"},
-			{"c:\\Hello\\..\\world\\", "C:\\Hello\\..\\world\\"},
+			{"c:\\Hello\\..\\world\\", "C:\\Hello\\..\\world\\."},
 			{"c:\\Hello\\..\\world\\foo", "C:\\Hello\\..\\world\\foo"},
 			{"c:\\\\Hello\\\\..\\world\\foo", "C:\\Hello\\..\\world\\foo"},
 			{"\\\\Server\\Share\\Hello\\\\..\\world\\foo", "\\\\Server\\Share\\Hello\\..\\world\\foo"},
@@ -213,25 +213,27 @@ func TestBuilder(t *testing.T) {
 			"./.":                                 ".",
 			"../":                                 "..",
 			"../.":                                "..",
-			"/.":                                  "\\",
-			"/./":                                 "\\",
-			"/..":                                 "\\",
-			"/../":                                "\\",
-			"/hello/.":                            "\\hello\\",
+			"/.":                                  "\\.",
+			"/./":                                 "\\.",
+			"/..":                                 "\\.",
+			"/../":                                "\\.",
+			"/hello/.":                            "\\hello\\.",
 			"/hello/../.":                         "\\hello\\..",
 			"//Server/Share/hello":                "\\\\Server\\Share\\hello",
-			"//Server/Share/.":                    "\\\\Server\\Share\\",
-			"//Server/Share/./":                   "\\\\Server\\Share\\",
-			"//Server/Share/..":                   "\\\\Server\\Share\\",
-			"//Server/Share/../":                  "\\\\Server\\Share\\",
-			"//Server/Share/hello/.":              "\\\\Server\\Share\\hello\\",
+			"//Server/Share/.":                    "\\\\Server\\Share\\.",
+			"//Server/Share/./":                   "\\\\Server\\Share\\.",
+			"//Server/Share/..":                   "\\\\Server\\Share\\.",
+			"//Server/Share/../":                  "\\\\Server\\Share\\.",
+			"//Server/Share/hello/.":              "\\\\Server\\Share\\hello\\.",
 			"//Server/Share/hello/../.":           "\\\\Server\\Share\\hello\\..",
 			"/\\Server\\Share/hello/../.":         "\\\\Server\\Share\\hello\\..",
-			"\\\\?\\C:\\hello\\.":                 "C:\\hello\\",
-			"\\\\?\\UNC\\Server\\Share\\hello\\.": "\\\\Server\\Share\\hello\\",
-			"\\??\\C:\\hello\\.":                  "C:\\hello\\",
+			"\\\\?\\C:\\hello\\.":                 "C:\\hello\\.",
+			"\\\\?\\UNC\\Server\\Share\\hello\\.": "\\\\Server\\Share\\hello\\.",
+			"\\??\\C:\\hello\\.":                  "C:\\hello\\.",
 			"\\??\\Z:\\file0":                     "Z:\\file0",
-			"\\??\\UNC\\Server\\Share\\hello\\.":  "\\\\Server\\Share\\hello\\",
+			"\\??\\UNC\\Server\\Share\\hello\\.":  "\\\\Server\\Share\\hello\\.",
+			"\\\\.\\C:\\hello\\.":                 "C:\\hello\\.",
+			"\\\\.\\UNC\\Server\\Share\\hello\\.": "\\\\Server\\Share\\hello\\.",
 		} {
 			t.Run(from, func(t *testing.T) {
 				builder1, scopeWalker1 := path.EmptyBuilder.Join(path.VoidScopeWalker)
@@ -445,6 +447,28 @@ func TestBuilder(t *testing.T) {
 		require.Equal(t, "\\\\myserver\\myshare\\data.txt", mustGetWindowsString(builder))
 	})
 
+	t.Run("DeviceNamespaceDrivePath", func(t *testing.T) {
+		scopeWalker := mock.NewMockScopeWalker(ctrl)
+		componentWalker := mock.NewMockComponentWalker(ctrl)
+		scopeWalker.EXPECT().OnDriveLetter('C').Return(componentWalker, nil)
+		componentWalker.EXPECT().OnTerminal(path.MustNewComponent("file.txt"))
+
+		builder, s := path.EmptyBuilder.Join(scopeWalker)
+		require.NoError(t, path.Resolve(path.WindowsFormat.NewParser(`\\.\C:\file.txt`), s))
+		require.Equal(t, "C:\\file.txt", mustGetWindowsString(builder))
+	})
+
+	t.Run("DeviceNamespaceUNCPath", func(t *testing.T) {
+		scopeWalker := mock.NewMockScopeWalker(ctrl)
+		componentWalker := mock.NewMockComponentWalker(ctrl)
+		scopeWalker.EXPECT().OnShare("server", "share").Return(componentWalker, nil)
+		componentWalker.EXPECT().OnTerminal(path.MustNewComponent("file.txt"))
+
+		builder, s := path.EmptyBuilder.Join(scopeWalker)
+		require.NoError(t, path.Resolve(path.WindowsFormat.NewParser(`\\.\UNC\server\share\file.txt`), s))
+		require.Equal(t, "\\\\server\\share\\file.txt", mustGetWindowsString(builder))
+	})
+
 	t.Run("RelativeDrivePaths", func(t *testing.T) {
 		builder1, s := path.EmptyBuilder.Join(path.VoidScopeWalker)
 		require.NoError(t, path.Resolve(path.WindowsFormat.NewParser("C:\\a\\b"), s))
diff --git a/pkg/filesystem/path/windows_format.go b/pkg/filesystem/path/windows_format.go
index 73fc3df8..1cf94f8b 100644
--- a/pkg/filesystem/path/windows_format.go
+++ b/pkg/filesystem/path/windows_format.go
@@ -60,24 +60,28 @@ type windowsParser struct {
 }
 
 func (p windowsParser) ParseScope(scopeWalker ScopeWalker) (next ComponentWalker, remainder RelativeParser, err error) {
-	// Handle extended-length paths starting with \\?\.
 	path := p.path
+	hasPrefix := false
 	if len(p.path) >= 4 && p.path[0] == '\\' && p.path[1] == '\\' && p.path[2] == '?' && p.path[3] == '\\' {
+		// Extended-length paths starting with \\?\.
 		path = p.path[4:]
-		// Handle \\?\UNC\.
-		if len(path) >= 4 && strings.EqualFold(path[:4], "UNC\\") {
-			return parseUNCPath(path[4:], scopeWalker)
-		}
+		hasPrefix = true
+	} else if len(p.path) >= 4 && p.path[0] == '\\' && p.path[1] == '?' && p.path[2] == '?' && p.path[3] == '\\' {
+		// NT object namespace paths starting with \??\.
+		// https://learn.microsoft.com/en-us/openspecs/windows_protocols/ms-even/c1550f98-a1ce-426a-9991-7509e7c3787c
+		path = p.path[4:]
+		hasPrefix = true
+	} else if len(p.path) >= 4 && p.path[0] == '\\' && p.path[1] == '\\' && p.path[2] == '.' && p.path[3] == '\\' {
+		// Win32 device namespace paths starting with \\.\.
+		// https://learn.microsoft.com/en-us/windows/win32/fileio/naming-a-file#win32-device-namespaces
+		path = p.path[4:]
+		hasPrefix = true
 	}
 
-	// Handle NT object namespace paths starting with \??\.
-	// https://learn.microsoft.com/en-us/openspecs/windows_protocols/ms-even/c1550f98-a1ce-426a-9991-7509e7c3787c
-	if len(p.path) >= 4 && p.path[0] == '\\' && p.path[1] == '?' && p.path[2] == '?' && p.path[3] == '\\' {
-		path = p.path[4:]
-		// Handle \??\UNC\
-		if len(path) >= 4 && strings.EqualFold(path[:4], "UNC\\") {
-			return parseUNCPath(path[4:], scopeWalker)
-		}
+	// Handle UNC paths following a namespace prefix
+	// (e.g. \\?\UNC\server\share or \??\UNC\server\share).
+	if hasPrefix && len(path) >= 4 && strings.EqualFold(path[:4], "UNC\\") {
+		return parseUNCPath(path[4:], scopeWalker)
 	}
 
 	if len(path) >= 2 {